2,4,6-Trimethylpyridine → HCID 20036331, compound

HRID 1904929Notes

Reaction equation

HRID 1904929 reaction equation
C[N:2]1[CH2:7][CH2:6][CH:5]([CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[CH2:19][CH2:20][N:12]([C:13]=34)[C:11]3[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=3[NH:9]2)[CH2:4][CH2:3]1.N1C(C)=CC(C)=CC=1C.[Cl:34]C(OC(Cl)C)=O>ClCCl>[ClH:34].[NH:2]1[CH2:3][CH2:4][CH:5]([CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[CH2:19][CH2:20][N:12]([C:13]=34)[C:11]3[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=3[NH:9]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 5213051-Chloroethyl chloroformateHCID 14459738HCID 14459738, compound

Product 1

HCID 20036331HCID 20036331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a 1 L, 3-necked round bottom flask equipped with a reflux condenser, nitrogen inlet, magnetic stirring bar and addition funnel were fed 6-(1-methylpiperidin-4-yl)-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (19.3 gm), collidine (622 gm) and dichloromethane (500 ml). The mixture was heated to a gentle reflux and alpha-chloroethyl chloroformate (19 gm) was added dropwise over a period of 30 minutes at refluxing temperature. The resultant solution was refluxed for 2 hours and thereafter cooled to about 50° C. The solution was concentrated to a solid-oil mixture and thereafter extracted with ether (about 2 L). The insolubles were filtered off and the ethereal solution was concentrated and dried on a rotary evaporator (high vacuum pump at about 80° C.) until little collidine was left. The crude product (43 gm) was identified as the bis-alpha-chloroethyl carbamate of the desired product.

Workup

  1. customTo a 1 L, 3-necked round bottom flask equipped with a reflux condenser, nitrogen inlet, magnetic stirring bar and addition funnel
  2. temperatureThe mixture was heated to
  3. temperaturea gentle reflux
  4. temperatureat refluxing temperature
  5. concentrationThe solution was concentrated to a solid-oil mixture
  6. extractionextracted with ether (about 2 L)
  7. filtrationThe insolubles were filtered off
  8. concentrationthe ethereal solution was concentrated
  9. dry with materialdried on a rotary evaporator (high vacuum pump at about 80° C.) until little collidine
  10. waitwas left

Sources & evidence

ORD record
ord-f6dc8480b52d41ceb474c50233efe694
Source dataset
uspto-grants-1989_06
Patent number
US04840947

Reaction notes

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